25 keys spread across a five-building Edgartown village estate built around the 1864 Captain Holmes House — Relais & Châteaux since 1990, owner Gery Conover's 50-year preservation project, and the only Relais property on Martha's Vineyard.
"25 keys in a restored 1864 Edgartown sea-captain's house — Relais & Châteaux since 1990, the only Relais property on Martha's Vineyard, and the most-considered single-property MV anniversary stay."
The Charlotte Inn occupies a five-building Edgartown village estate built around the 1864 Captain Holmes House — the original 1864 sea-captain's residence built by Captain Samuel Osborn for his daughter Charlotte Osborn Holmes (the property's namesake). The estate has been the 50-year preservation-and-restoration project of owner Gery Conover, who acquired the original Holmes House in 1971 and continuously expanded the property across the four adjacent buildings (the Carriage House, the Coach House, the Garden House, and the Summer House) over the following five decades. The Charlotte Inn was admitted to Relais & Châteaux in 1990 and remains the only Relais & Châteaux property on Martha's Vineyard or Nantucket.
The 25 keys are spread across the five buildings of the Edgartown village estate. Categories run from entry-tier Garden House Rooms (24 sqm in the smaller annex buildings) through Carriage House Suites (40 sqm with restored period architectural details) to the named Captain Holmes Suite (60 sqm — the original 1864 master bedroom of the Holmes House, with private fireplace, sitting room, and the only original 1864 four-poster bed in the property). Every room is individually decorated with antique period furniture sourced through Conover's 50-year auction-house contacts — no two rooms hold the same wallpaper, fabric, or furniture scheme, and the Conover-curated decorative inventory rotates across the property as new pieces are added or restored.
Operationally The Charlotte Inn runs the smallest-Relais-property scale at the Edgartown-village register. The Cellar Restaurant — the in-house fine-dining venue inside the original 1864 cellar of the Holmes House — runs the contemporary-American tasting register that the Charlotte Inn kitchen team has built over four decades. The kitchen sources from MV's working farms (Morning Glory Farm, Beetlebung Farm, the seasonal Vineyard fishing-boat partnerships) and runs a 6-course tasting menu that books three weeks ahead for any high-season weekend. The wine cellar runs about 200 bins focused on Burgundy and California vintage with a small Chappaquiddick-vineyard sub-list. The Rosé Garden (the property's central outdoor courtyard) runs the breakfast-and-afternoon-tea programme.
What gives The Charlotte Inn the structural Martha's Vineyard luxury position is the only-Relais-on-MV combination at the Edgartown-village walking scale. The Edgartown harbor, the Edgartown Lighthouse, the Vineyard Trust historic-museum cluster, and the Old Whaling Church are all within 5 minutes' walk of the property; the Chappaquiddick-ferry On Time II is 3 minutes' walk; and the South Beach (the calm-bay swimming beach) is a 12-minute drive. The 25-key footprint and the Conover-family service signature give a level of personal-attention that none of the larger MV alternatives can replicate. For a Martha's Vineyard anniversary or honeymoon that wants the smallest-luxury-property scale and the only Relais & Châteaux register on the island, the Charlotte Inn is the only choice that combines all four.
The Captain Holmes Suite — original 1864 master bedroom with private fireplace, sitting room, and the only original 1864 four-poster bed — is the milestone unit. Anniversaries at The Charlotte Inn are typically structured around three to four nights with a Cellar Restaurant tasting evening, a Chappaquiddick-and-South-Beach day trip, and a private afternoon-tea programme in the Rosé Garden.
The Carriage House Suites — 40 sqm with restored period architectural details — are the standard MV honeymoon unit at The Charlotte Inn. Pair five nights at The Charlotte Inn with two nights at a Nantucket property (White Elephant or the Wauwinet) for the standard Massachusetts-island-pair honeymoon arc.
27 South Summer Street
Edgartown, MA 02539
United States
27 South Summer Street — Edgartown village core, walking distance to harbor, Lighthouse, and Chappaquiddick ferry
25 keys across 5-building Edgartown village estate
Garden House Room: 24 sqm in smaller annex buildings
Carriage House Suite: 40 sqm with period details
Captain Holmes Suite (signature): 60 sqm 1864 master bedroom
Each key individually antique-furnished
From USD 580/night Garden House Room
Check-in: 4:00 PM
Check-out: 11:00 AM
Conover family ownership since 1971 (54 years)
Relais & Châteaux since 1990
Open May-October; ferry from Woods Hole 45 min
Only Relais & Châteaux property on Martha's Vineyard
1864 Captain Holmes House preserved
5-building Edgartown village estate
Cellar Restaurant fine-dining tasting menu
Rosé Garden afternoon-tea programme
Walking distance to Edgartown harbor and Lighthouse
Free WiFi throughout
From USD 580/night for entry-tier Garden House Rooms; Carriage House Suites from USD 1,200; Captain Holmes Suite from USD 2,400. The Charlotte Inn is open May-October only and books five to seven months out for the Memorial Day-Labor Day high season; the May-June and September-October shoulder windows carry the most-considered rate-to-experience ratio.
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